Between Poker Night 1 and Poker Night 2 I won the Dangeresque Shades (Demoman cosmetic), Liscense to Maim (all classes cosmetic), Lugemorph pistol (for Scout and Engineer), Enthusiast's Timepiece (Spy watch), Iron Curtain (Heavy's gun that he bought in with), Dapper Disguise (Spy cosmetic), Samson Skewer (Brock samson's Bowie knife, as a cosmetic for Heavy), Necronomicrown (Pyro cosmetic), Bloodhound (Sam's hat, cosmetic for Sniper and Spy), and the Long-fall Loafers (Scout cosmetic).

I did win Glados's paranoia personality core in poker night 2.

Portal reference?